Fintech Chatter: Conversations with Fintech Leaders

After receiving great feedback on our LinkedIn posts this year, Dexter has decided to record a weekly rant sharing his thoughts and insights on leadership, careers and Fintech.

In this very first episode, Dexter discusses the impact of AI on the job market, AI is indeed replacing jobs rather than just augmenting them. 

He highlights the shift in focus from hiring based on technical skills to leadership capabilities, reflecting a broader trend in Fintech. Dexter also provides insights on how professionals should adapt their experience to remain relevant in a rapidly changing industry.

Takeaways

• AI is replacing jobs, not just augmenting them.
• Fintech companies are thriving with fewer employees.
• The focus is shifting from skills to leadership capabilities.
• Leadership can come from any background or demographic.
• Every hire should embody leadership qualities.
• Experience should be framed around problem-solving.
• The next 20-30 years will differ significantly from the past.
• Diversity in leadership is essential for success.
• Adapting resumes to highlight relevant experience is crucial.

If you enjoyed this format send us a message.

You can check out the episode with Paul Roos on Leadership - https://tieronepeople.com/2025/01/21/paul-roos-building-high-performance-cultures/

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About this Episode

Dexter Cousins interviews Craig Carroll, co-founder of JustFund, one of Australia's fastest-growing startups.

Craig shares their innovative approach to solving a problem that creates untold stress on those seeking divorce - lending for family law fees.

With a background as a serial entrepreneur, Craig shares insights on navigating uncertainty, his lessons learned from the US market, the importance of company culture, and the role of AI in enhancing client service.

Dexter gets to discuss his favourite topic - hiring the right talent and building a strong company culture as JustFund prepares for international expansion.


About Craig
 
Craig is passionate about financial services, education and technologies that either promote economic well-being and/or address societal challenges. Craig's career has been focused on creating, building and managing teams, raising capital, consumer social lending, product development, software development, corporate strategy and general management across various sectors.

Craig has extensive experience developing services that help individuals deal with financial matters. He has also advised educational institutions on admission strategies and accessibility. Throughout his career, Craig has been an investor and advisor to various early-stage and growth companies.


Key Takeaways

• JustFund has approved about $115 million in lines of credit since its inception.
• Lessons from the US market -the importance of controlling customer acquisition costs.
• JustFund focuses on client-centric solutions for individuals facing family law issues.
• The cultural differences between the US and Australia have a major impact on business strategies and operations.
• How AI can enhance productivity and client service in the lending process.
• Hiring for adaptability and resilience is crucial in a startup environment.
• Building a strong company culture from day one is essential for long-term success.
• JustFund's plans to expand into international markets, starting with New Zealand.

Chapters

00:00 Introduction to JustFund and Its Mission

03:24 Innovating Financial Products Using Data

06:36 The Role of AI in Product Development

12:17 Rapid Growth and Scaling Strategies

19:26 Craig's Experience in the USA

23:32 Australian vs US Talent

27:40 The Challenges of Hiring in 2025

31:36 Setting the Foundations of Culture

36:35 The Benefits of Being Obsessed with NPS

Links & Resources:

• Visit JustFund website
• Connect with Craig Carroll 
• Connect with Dexter Cousins
• Learn more about Tier One People

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In this special episode of Fintech Chatter, host Dexter Cousins speaks with Paul Roos, AFL legend and founder of Performance by Design. They explore the parallels between elite sports and startup culture, discussing how founders and leaders can build high-performance teams on a budget!

About Paul
 
Paul shares insights from his trophy-winning coaching career, steering the Sydney Swans to their first title in 72 years! The culture Roosy built at the club is still legendary 20 years later. He's spent the past decade advising startups and executives at some of Australia's largest companies on building high-performing cultures and unique challenges faced by Fintech founders.

In the interview Dexter and Paul discuss the importance of self-awareness, the role of leadership in shaping culture, and the challenges startups face as they grow. The conversation also touches on the significance of health and wellbeing in leadership, and how small companies can create a positive culture that drives success.

Key Takeaways

• The culture built at the Sydney Swans is a model for startup success.
• Leadership behaviours directly influence organisational culture.
• Self-awareness is crucial for effective leadership.
• Startups must define their culture early to avoid fragmentation.
• Investing in culture can prevent costly turnover.
• High-performance teams require clear role definitions.
• Remote work challenges can be overcome with a team-first mindset.
• Health and well-being are essential for leadership effectiveness.
• Leaders should model the behaviours they want to see in their teams.
• Incremental changes can lead to significant improvements in culture.

Chapters

00:00   Introduction and Guest Background
04:38   Transition from Sports to Corporate Culture
09:30   Building a High-Performance Culture
14:11      Leadership and Self-Awareness in Startups
18:44    The Importance of Foundational Culture
23:25    Role of Leaders in Shaping Culture
27:16     Navigating Growth and Leadership Challenges
30:13    The Shift to Remote Work and Team Dynamics
33:11     Hiring for Culture and Team Cohesion
36:32   The Importance of Defining Company Culture
39:07   Mental Health and Personal Wellbeing in Leadership
42:02    Looking Ahead: Commitment to Growth in 2025

Links

Visit Performance by Design website

Connect with Paul Roos

Connect with Dexter Cousins

Learn more about Tier One People

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About this Episode
Dexter Cousins welcomes Rob Lincolne, Founder & CEO of PayDock to the latest episode of the Fintech Chatter Podcast.
Rob shares Paydock's unique position in the payments ecosystem with a deep-dive into payments orchestration and the importance no-code solutions.
He discusses the challenges of attracting top talent, and the complexities of building a global team. He highlights the resilience his team in Ukraine who have operated under tough conditions since 2022.
Rob shares with Dexter his daily routines and the importance of maintaining a healthy work-life balance as a founder of a global Fintech venture.

About Rob Lincolne
Rob Lincolne is an accomplished entrepreneur with extensive experience in the payments industry. Founder and Co-CEO of Paydock, he is dedicated to transforming how we transact by creating the world’s most trusted payment orchestration platform.
His journey began in Sydney 2007 when he founded a digital marketing agency specialising in the not-for-profit sector.
The Paydock vision arose from the need for better integration between financial institutions and their merchant clients. Their innovative approach aims to unlock the fintech market's true benefits.
Rob has also founded a successful "near-shore" talent placement agency in Ukraine, connecting software engineers with fintechs around the globe.

About Paydock
Paydock is a payments orchestration platform, leading the way in resolving costly merchant issues with its innovative API-first technology that harmonises payment, fraud, identity and other vendors (such as Stripe, PayPal, etc.) through a single interface.

Key Takeaways

• PayDock addresses the technology gaps between large banks and fintech.
• Adopting a no-code solution within the payments industry is essential for merchant adoption of fintech.
• Orchestration should be about enabling merchants, not commoditising services.
• Building a global team has been crucial for scaling the business.
• Customer relationships are vital in the fintech space.
• The future of payments is modular and interoperable.
• Attracting talent requires offering challenging problems to solve
• Character and resilience are more important than skills.
• The hype in fintech is over; it's time for real business.

Chapters
00:00  Introduction to Fintech Chatter
01:59   Understanding PayDoc and Its Unique Position
06:06  Innovation and the No-Code Approach
10:58   Defining Payments Orchestration
14:58   The Journey of PayDoc: From Australia to the UK
19:09   Building a Global Team and Talent Acquisition
21:54   Supporting Teams During Crisis: The Ukraine Experience
25:32   Attracting Top Talent in Fintech
29:26   The Importance of Character in Hiring
33:56   Resilience and Overcoming Adversity
38:33   Current Trends in Fintech
42:14   Daily Routines and Habits of Founders
45:06  Looking Ahead: PayDoc's Future

Links
Visit Paydock
Connect - Rob Lincolne
Connect - Dexter Cousins

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Fintech Chatter is brought to you by Tier One People - the executive search firm dedicated to connecting high-growth fintech companies with exceptional leadership talent.

About this Episode

In the latest episode of Fintech Chatter, host Dexter Cousins chats to Simon Schwarz, Co-Founder and CEO of FreightInsure, about his journey from fintech to insurtech.

Simon shares how his career from investment banking, to fintech, to insurtech (working with SocietyOne, Zip and BizCover along the way) has shaped his current scaleup, FreightInsure.

We take a deep dive into Simon’s strategy to build FreighInsure and how the MGA (Managing General Agent) model has enabled the distribution of embedded insurance products.

Simon reflects on the dual responsibilities as Co-Founder and CEO, and his life hacks for balance and well-being. 

About Simon
Simon is the Co-Founder and Managing Director of FreightInsure, Australia’s leading platform for embedded freight insurance. 

He started his career at Investec Bank in Australia, holding roles as Head of Investments, Head of Credit and Head of Board Risk and Capita. Simon has sat on boards as a Non-Executive Director and Chairman at several investee companies.  He has also acted on advisory boards at Zip Co and Middle, and is a Board member of Insurtech Australia and the Regulatory and Compliance Working Group.

Simon is a graduate of the Australian Institute of Company Directors, holds an MBA (Exec), Masters of Applied Finance, and is the recipient of the University Medal for pure mathematics from the University of Sydney. He was an Honorary Fellow at Macquarie University’s Applied Finance Centre and a member of the  Menzies School of Health Research Development Committee. 

About FreightInsure
FreightInsure offers embedded goods-in-transit insurance directly from a transport company's booking platform. Shippers no longer need to buy annual marine insurance policies, but can simply purchase insurance on a needs basis, when booking their freight, within less than a minute.

Key Takeaways

• How the MGA model allows for rapid growth without the need for capital reserves
• How distribution innovation is big Insurtech opportunity
• How AI applications are being developed to enhance underwriting processes
• Freight and logistics market isn’t sexy but it presents vast opportunities for growth
• Identifying profitable market opportunities is crucial for business success
• The quality of founders is the key to a startup's success
• Focus on distribution to solve market problems effectively
• The role of a founder differs significantly from that of a CEO
• InsurTech in Australia is gaining momentum and attracting capital

Chapters
00:00 Introduction

05:54 The Birth of FreightInsure

12:01 Innovation in Distribution

17:57 Future Innovations and AI Applications

25:15 Identifying Market Opportunities

30:54 The Dual Role of Founder and CEO

39:00 The InsurTech Landscape in Australia

Links & Resources:

• Visit FreightInsure website
• Connect with Simon Schwarz
• Connect with Dexter Cousins
• Learn more about Tier One People

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About this Episode

In Episode 198 of the FintechChatter podcast, Dexter Cousins chats with Joel Yarbrough, CEO of Moment. Joel, an OG fintech leader, discusses his global journey with roles at PayPal, Grab, and now Moment, where he's tapping into Africa's fintech opportunities.

Dexter and Joel discuss the qualities of successful individuals in startup environments, emphasizing the importance of passion, collaboration, and a growth mindset.

Joel talks about the Importance of giving back and building diverse teams, as well as the challenges of hiring in a rapidly changing market. He also provides insights into the future of Moment and the importance of being mission-driven in the business world.

About Joel
A passionate leader whose love of technology drives him to deconstruct complex systems and rebuild them to solve real problems. He has spent most of my career helping strategise, design, product manage, and deliver multi-channel solutions in and around the intersections of financial services, commerce, and technology.

He would describe himself as a great evangelist and dot connector, working with partners to understand their strategies and solve their problems. The delight of leading product teams to make the vision a reality is a real joy.

His core belief is that together we can make the world a better place - even if it's through our own enlightened self-interest. By doing things well, and being decent to each other we will all keep pushing to a brighter place together.

About Moment
Moment is an integrated payments platform for Africa, incubated as a joint venture by MultiChoice, Rapyd, and General Catalyst. We connect businesses and consumers in over 40 African countries. We're able to do so through our broad network that aims to cover over 100 payment providers, 200 local payment methods, and 40 currencies.

Key Takeaways

• How Africa's projected population growth presents unique opportunities for fintech.
• Moment's aims to build a comprehensive payment network for Africa, as the trend towards digital payments grows. 
• Regulatory changes are shifting towards enabling innovation rather than just consumer protection.
• Australia's fintech scene is strong but needs to leverage its geographic and cultural assets more effectively.
• Regional trade clusters are more valuable than cross-oceanic trade relationships.
• The gig economy has empowered individuals in emerging markets, changing their economic prospects.
• The diversity in teams provides greater problem-solving capabilities and drives a growth mindset for individuals.
• Navigating hiring challenges requires clear communication to achieve high standards and cultural fit.
• Giving back creates a positive network effect and greater sense of fulfillment.

Chapters
00:00.  Introduction to Joel Yarbrough and Moment

05:42.  The Unique Opportunity in Africa's Fintech Landscape

14:01.  The Impact of Fintech on Personal Agency

19:44.  Australia's Fintech Identity and Global Positioning

25:08.  Understanding Human Capital in Startups

30:32.  Passion vs. Mission-Driven Work

39:01.  Navigating Hiring Challenges in a Changing Market

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Dexter Cousins shares an update from Tier One People with some exciting news on Executive hires.

And a snippet from a fantastic podcast episode with Joe Yarbrough, CEO of Moment.

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About this Episode

In episode 198 of the Fintech Chatter Podcast, host Dexter Cousins reconnects with Liam Millward, CEO and Co-Founder of Instant. They discuss the remarkable growth and evolution of Instant since their last conversation. Liam shares insights on shifting from a product-focused mindset to a revenue-driven approach, navigating challenges in a competitive landscape.

He shares the importance of building a high-performance team. Liam emphasises the significance of leadership, decision-making, and the role of personal experiences in shaping his entrepreneurial journey. The conversation also touches on the future of Instant and the strategies for market expansion.

The Instant Journey 

As CEO and Co-founder of Instant; Liam is on a mission to power the world's most innovative brands, helping to drive their revenue and retention on autopilot. He launched his first funding round led by Blackbird, at age 17, generating $7.5m, the biggest pre-seed to date in Australia. 

As the business grew to $1.5m in annualised revenue, they have raised an additional $30m across Seed and Series A rounds. Hitting a healthy 1 million shoppers within 12 months of their launch.

Since Instant launched its Checkout product, they have gone on to develop Audiences and Targeting offering their 3 product across the US and Australia. 

This is a triple-pronged approach to customer retention and greater outcomes for business revenue.

About Liam Millward 

Liam started his first venture aged 13 in a caravan, travelling around Australia and the world with his family. His love of travel resulted in him curating and developing a well-known travel magazine, Navigate Australia with a monthly readership of 50,000+.

Key Takeaways

• Liam Millward reflects on the rapid growth of Instant since its inception.
• The importance of focusing on revenue rather than just product development.
• Building a strong sales strategy is crucial for startup success.
• Creating a high-performance culture is essential for team motivation.
• Leadership requires transparency and accountability within the team.
• Identifying and nurturing talent is key to sustaining growth.
• Travel and personal experiences can significantly influence an entrepreneurial mindset.
• Having a clear vision can inspire teams to achieve ambitious goals.
• Market expansion requires understanding and adapting to new environments.
• Failing as a company is not an option; resilience is vital.

Chapters

00:00 Introduction to Instant and Liam's Journey

05:28 Shifting Focus: From Product Obsession to Revenue

11:04 Sales Strategies for Rapid Revenue Growth

16:40 Leadership and Transparency in Startups

22:27 Creating an Inspiring Vision for the Team

27:00 High Performance Work Environments

34:26 The Impact of Life Challenges on Entrepreneurship

42:13 Setting Ambitious Goals

49:14 The Realities of Starting a Business

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About this Episode

In Episode 196 of the Fintech Chatter podcast, Dexter Cousins is joined by Graham Strain, Co-Founder of Citoplus a digital platform for commercial broking. 

The Citoplus Journey 

Dexter and Graham look back at their first meeting and discuss Graham's journey from traditional Banking to Start up. His recognition that he was a transformation guy at heart and wanting to do "cool stuff for customers" was the driver behind founding Citoplus. 

He chats about support from great shareholders, and how they funded Citoplus through, what he calls the "Friends, Families & Fools" model, who have shown great faith in their vision. 

Graham outlines the plans for the future and how Citoplus aims to reach 100% of the digital broking market through partnerships with Banks and Non-Banks. Watch out for lots of new announcements. 

About Citoplus

CitoPlus is the cornerstone of modern, frictionless commercial lending. Designed by industry leaders, they launched a product that streamlines the laborious process of SME lending.

Citoplus has focussed on removing the paperwork-heavy process through automation. The result is a broker-friendly data-rich system that delivers better client service and achieves quicker outcomes, meaning deals are closed faster.

About Graham Strain

As Co-founder of Citoplus, Graham has a background in banking, including 13 years at NAB in product, business bank and corporate development executive roles. He held the position of interim CFO and Product Head at start-up Angle Auto Finance, an asset finance company. He was GM - Business Products at Judo Bank in the SME lending space.

Chapters:

00:01:15 Citoplus The Journey and Solution 

00:19:45 Graham's Backstory and Career in Banking 

00:25:20 Why Startups and Banks are so different 

00:39:00 Big News from Citoplus

Links & Resources:

• Visit Citoplus website
• Connect with Graham Strain
• Connect with Dexter Cousins
• Learn more about Tier One People

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In this special episode of Fintech Chatter, host Dexter Cousins and guest Kristofer Rogers of Volt.io discuss the Singapore Fintech Festival 2024, highlighting its scale, the quality of discussions, and the global interest in fintech.

They explore themes of financial health, geopolitical impacts, interoperability, and the future of embedded finance emphasizing the need for collaboration in the fintech ecosystem.

In this conversation, Kristofer Rogers and Dexter discuss the evolving landscape of FinTech, focusing on the implications of disruption, the changing nature of leadership, and the critical importance of talent.

They explore the accessibility of industry leaders, the significance of community events, and Australia's position in the global FinTech arena.

The discussion highlights the challenges and opportunities facing Australia, the need for a long-term vision, and an optimistic outlook for the future of FinTech, particularly in relation to trade finance and digital currency.

2024 Singapore Fintech Festival Highlights

1. The Singapore Fintech Festival 2024 had 65,000 delegates.
2. Financial health is a more pressing issue than financial inclusion.
3. Interoperability is becoming more important than innovation in fintech.
4. Africa presents unique opportunities for fintech.
5. Collaboration among fintechs and banks is essential for success.
6. Embedded finance is maturing, but challenges remain.
7. The festival highlighted the importance of genuine business connections.
8. Talent is a critical focus area that is often overlooked in discussions.
9. Accessibility of industry leaders fosters networking and collaboration.
10. A long-term vision is necessary for Australia to establish its identity in FinTech.
11. Optimism exists for the future of FinTech in Australia, with potential growth opportunities.
12. Global trade and currency are poised for significant changes in the coming years.
13. The FinTech landscape is evolving, and businesses must adapt to stay relevant.

Chapters

00:00 Overview of the Singapore Fintech Festival
06:04 Global Perspectives on Fintech
12:01 Interoperability vs. Innovation in Fintech
18:00 Collaboration in the Fintech Ecosystem
27:46 The Implications of Disruption
33:21 Accessibility and Networking in FinTech
40:05 Challenges and Opportunities for Australia
45:55 Optimism for the Future of FinTech

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